Elena: We have a situation.
Damon: Of the Doppleganger variety.

Elena, meet Crazy Pants. Crazy Pants, meet Elena.

It's called being secure. I can tell you believe in that by the way you wear your hair.

Put the damn crossbow down, Pocahontas.

Tessa: Buy you an I'm sorry drink?
Damon: More like an I'm sorry keg.

Guilt. Don't know it, but I've heard it can be a royal bitch.

Why do you suck so badly at killing yourself?

I don't speak crazy person Jer, you're gonna have to translate that for me.

You took one philosophy class and now you're the queen of nature versus nurture?

Stefan: Katherine took the Cure?
Damon: You have a lot to catch up on, Stefan.

Play nice. Or I'm gonna revisit the deep, dark well idea.

I know I said it doesn't bother me that you have a psychic connection to your ex-boyfriend, but I don't need the play by the play.

Vampire Diaries Quotes

You want a love that consumes you. You want passion and adventure, and even a little danger... I want you to get everything you're looking for. But for right now, I want you to forget that this happened. Can't have people knowing I'm in town yet. Goodnight, Elena.

Damon

You are literally the best person I've ever known. And for me to think I could ever change you was giving me way too much credit and you way not enough… you're the good. And I need a little good in my life.

Damon [to Elena]